


Grace in Heels

by Anonymous



Category: Infinity Train (Cartoon)
Genre: Bondage, Clothing Kink, Cock & Ball Torture, F/M, Face Slapping, Femdom, High Heels, I think that's enough tags for ya'll to get the point, It's porn, Masochism, Riding Crops, Sadism
Language: English
Status: Completed
Published: 2021-01-22
Updated: 2021-01-22
Packaged: 2021-03-14 04:15:09
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 1
Words: 4,080
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28914465
Author URL: https://archiveofourown.org/
Summary: Sometimes, when things started to get stressful for her, Grace would request that Simon help her 'work out the frustration.'
Relationships: Simon Laurent/Grace Monroe
Kudos: 7
Collections: Anonymous





	Grace in Heels

Sometimes, when things started to get stressful for her, Grace would request that Simon help her 'work out the frustration.' They'd done this often enough that now it didn't fluster Simon too badly as she bound his hands together in the back of an empty, damaged storefront. Then she threw the rope over an exposed ceiling beam, pushed Simon to his knees, and tied off the excess length, pulling hard as she did so that his arms were being hoisted high above his head. For his part, Simon went along willfully with this. He was made to kneel high, so that both his arms and thighs had to endure the strain of holding himself upright. For now, it didn't hurt too bad, but he knew that his endurance would wear down as this went on. She'd make sure of that, had tied him up in this way for that express purpose. He watched as she walked away and out of sight into the back area of the store. Simon was left hanging for a long time, at least a half-hour or more it felt. Instinct drove him to test the binding, squirm around and shuffle awkwardly on his knees as his wrists twisted. It held fast, so after a worthless attempt at getting free Simon gave up and just tried to make himself comfortable.

She usually didn't take so long to get ready... but he understood the hold up as soon as she reappeared. She held the crop loosely in one hand, as usual. She'd also changed into a different outfit, though. Simon felt his whole body abruptly go hot with excitement as he drank in the view. A cropped top and short skirt left her shoulders and trim waist exposed. She wore long gloves, as she generally did- but these were a different pair, chosen to match the rest of her outfit. What really drew Simon's attention, however, was what she'd chosen to put on below the skirt. Sheer white thigh-high stockings left a strip of skin visible between the end of those and the start of her skirt, and the tall heels she wore only helped to make her tower further over him as she approached. She'd applied a shimmering lotion to her body before putting the clothing on, which made her skin glimmer like a goddess in the low light as she moved. Her expression was severe, dead-pan and blank, as she regarded Simon coolly while she stood before him. She appraised with detachment the way he gazed up at her with eager expectation. It was the same cruel, dark stare she gave to captive nulls as she determined whether they were worth keeping around. Most nulls were ultimately cast to the wheels. As he gaped upward in a drunken stupor, he further realized that at this angle it was far too easy to peer up the loose bottoms of both her skirt and top. He couldn't help but stare at the undersides of her bra and panties. The plain white undergarments matched her stockings and gloves. His face started to glow with a furious blush, his expression dropping into a wordless plea. In response, Grace frowned and folded her arms under her bust, blocking that view. She suddenly looked uncomfortable, almost shy about the way she was dressed. Her thighs pressed together, before she sharply commanded, "Stop looking at me like that."

Simon obediently dropped his gaze. Not that it helped, because he still could and would stare at her calves, thick with muscle and swathed in soft nylon, as they tapered into thin, pretty ankles. Not to mention the heels- Simon's eyes greedily traced the contours of how they hugged around the shape of her feet, holding her heels up with a thin, tapered, almost spike-like support. She stepped around and shifted so naturally while wearing them, without a hint of clumsiness. She walked around him now, and once again moved out of sight as she went behind him. He didn't dare turn around to see what she was doing, as that was already a well-learned rule. His ears could only pick up the lack of sound from her heels as she paused. He didn't hear it coming when she leaned over, not until he could feel her pulling up the back of his hoodie. She pulled at the tank top beneath as well, untucked it from his pants, and folded both articles of clothing up over the top of his head. It partially blindfolded him and more importantly left his back bare and exposed. He instinctively braced himself for the first blow, and then consciously forced himself to relax when it wasn't immediately forthcoming.

As soon as the tension visibly drained, of course, that's when she first struck. The bite of the crop landed across his upper back, and immediately Simon jerked and clung to the rope that held him upright, swaying with the impact. After that, the blows began to fall in quick, rapid succession. Simon found himself losing his breath with the ferocity of the constant abuse. He could barely whine, but before long a line of tears were dripping to his chin and his shoulders wracked with breathless sobs. He clung to the rope, his only lifeline, as his whole being condensed into one bright point of pain. The cruel, divine laughter of Grace's momentary amusement rang in his ears as he was beaten mercilessly. His back grew hot, and more than once he was left wondering if she'd drawn blood, if the welts were also decorated with cuts and tears. Even if they were, it didn't seem to concern her, as she applied the same level of violence over and over again to his flesh.

She only stopped once she was audibly panting with exertion, and her senses had begun to finally return to her. Simon was quivering, silent except for his shaky breaths as he bowed forward. The crop had both bruised and broken the fair skin on his back. At the first sight of it, Grace felt momentarily ashamed of herself for once again succumbing to her urges. After staring a bit longer at the way Simon had quietly endured the undeserved punishment though, she ultimately convinced herself that it was his fault. He allowed it, relished in receiving such treatment in fact. She hit him once more as she decided upon it, and this time a quiet little whimper and flinch answered the strike since he had been given a brief respite before it happened. "You're pathetic," she spat. Simon shook but didn't verbally respond. "I see the way you look at me, you little worm. You're so predictable, so easy. You actually like this, don't you?" Still, he remained silent, so Grace boxed him on the ear hard enough that his head rang, and he yelped again at the unexpected swing. "I'm asking you a question!" she insisted as she did so.

"I'm sorry," Simon first said, which earned him another blow on the other side of his head.

"Answer the question!" Grace demanded. Simon shook his head, the headspace he'd sank into had obliterated his short term memory and he couldn't remember the question now that the dull ringing in his skull had become a constant feature. "Ugh," Grace scoffed as she picked up on his sense of hazy confusion, "I can already tell the answer anyway. You sick dog. Let's see how much you like this..."

Another series of lashes rained down on his back, Grace huffed with the force she put into each swing of the crop. They'd picked that particular tool up from a horse-racing car that had fallen to one of their raids, and it had been designed for use on livestock- which meant it was more than brutal when used against the comparatively fragile hide of another human. That didn't concern her at all, though, as she applied the tool turned weapon against his back a few more times, hard enough to spill blood. It delighted her senses when the faint coppery scent finally reached her nose, and only then did she settle again. She saw that Simon was starting to lose his strength as well. At first, he had been kneeling tall and proud, with only the slightest forward bow as he had accepted the initial lashes. But now he sagged weakly, his thighs were burning and he was trying to go lax as he swung from the overhead bindings. The rope around his wrists prevented him from sitting down fully, and hanging his weight from there yanked on and twisted at the muscles in his arms. "Grace, I can't... No more, please," Simon spoke, his voice watery with pain as he teared up even more than before, staring at the ground with a miserable yet somehow dreamy frown.

At the sound of his broken tone, Grace sighed in mocked sympathy. Her heels clicked on the tiled floor, announcing the movement as she walked around him again. The tips of her heels came into view and once more Simon was enraptured with the sight. She had such small, dainty feet, but they somehow looked threatening and imposing in such well-crafted, physically demanding shoes. Then she deigned to kneel in front of him, her strong legs shifting majestically beneath the nylons as she did. She pushed the clothing that had been pulled over his head back so that they could fully see one another. Simon winced as the tanktop fell down his raw back, the sensation making him hyperaware of the hot welts that were already sweltering beneath the fabric that now covered them. Grace observed the state he was in, the way his eyes shined with tears and he shuddered with the effort to keep holding himself up. She hummed, then cupped his face in both hands and wiped his tears away. "Quit crying, you big baby."

"Are we done yet?" Simon asked, timidly. He still couldn't stop tearing up, but that meant that Grace had to keep her hands on him, had to keep swiping her thumbs under his eyes to catch the drops that escaped. The contact felt electric, such an intimate kindness after being the cause of his distress somehow made the cycle feel complete, at least to Simon. Grace, though, simply grinned slyly at the plea that had been disguised as a question.

"No, we're not. I've been under a lot of stress lately, with all the new recruits." Grace stood again, and Simon kept his gaze to the ground, lest he incurred her wrath by staring too intently again. Her stance shifted to indicate she had a hand on her hip as her lecture continued, "Not that you'd know, holed up in your room all the time." She reached for the other end of the rope, where it was tied to the overhead beam, and loosened the knot to slide it higher, giving Simon just enough slack to kneel down fully. Simon didn't immediately sit down, though, despite his trembling weakness, unsure of her intentions now. He nearly did melt at how close she had to stand to reach the rope but forced himself to only stare at her heel-clad feet even when the bottom of her skirt brushed against the top of his head. As she tightened the knot in its new position, she added, "Whenever you do come out, all you do is stare at me. It's annoying."

She finally just placed her foot on his thigh and used it to shove him down, the heel biting into his flesh as she did so. He sat back, but even then she kept leaning her weight onto the heel that was now digging against his leg. The only reason it didn't cut was the buffer of his pants, but it still bruised. He tried to move, tried to get his leg out from under her heel, but she wouldn't allow even a moment of relief, and would only press down harder as a punishment. Simon finally tried to gaze upward, in order to plea for her to stop. The words on his tongue died as soon as his gaze met her panties. In order to step on him, her skirt had lifted and her thick thighs had parted, allowing him an unrestricted view. Her body filled out nicely in the hips, and her thick inner thighs looked so soft and warm, brown skin providing a pleasing contrast against the white fabrics that clung tightly to her form. She loomed close enough that there was even a faint scent. A warmth came over Simon as his mouth went dry with want. When she turned her ankle in order to twist the heel into his leg, instead of whining or crying, Simon let out a needy moan. Grace snarled and gave his leg a parting stamp before she stopped. She stood before him on both feet again, sturdy and strong compared to the way Simon swayed and shuddered as he kneeled before her.

"You're actually starting to get off on this. Is it because of what I'm wearing?" she asked, in a decidedly derisive tone, as she crossed her arms and drew her legs together once more, in order to obscure his view of her undergarments. Simon hung his head in shame, too embarrassed to answer. Knowing that he was expected to, it didn't surprise him when she stomped at his other leg after he failed to respond. "Pathetic weirdo. You'd even let me throw you to the wheel, as long as I was dressed like this. Wouldn't you?"

Simon withered beneath the cruelty of what she spoke of. He heaved a heavy sigh and finally cast his eyes to the side, not even allowing himself to look at her heels, at her pretty ankles covered in white nylon. He missed the sight immediately and began to shiver. A fresh trail of tears started to roll down his face at the loss. "I'm sorry," he mumbled. He truly was, for both the way he had inadvertently worsened her oncoming mood by being a hermit, as well as the way his body had started to react to her cruelty, the last few times they'd done this together. The first sessions had been confusing, purely painful and upsetting as she struck him with anything that could serve as a switch to satiate her budding sadistic urges. That's why the bondage first came into play, in order to contain and control his meager attempts to escape her wrath. By now, it was simply part of the ritual, and as Grace had implied she knew he'd no longer avoid the treatments, even if he wasn't literally bound to accept them.

"You're sick, Simon, for letting me do this. How am I supposed to respect you, when I know just how weak you are?" she questioned. Her smile grew thoughtful and cruel, as she wondered aloud to herself, "Maybe I'll actually do it- I'll tell the kids to come grab you, and I'll watch as they throw you off. I wonder if you'd become a stain on the wheel, or if you're too small and insignificant to even leave that much of a mark." Simon looked crestfallen at the dismissive nature of her declaration but seemed unsettlingly resigned to the fate as well. "You would let me do that, of course. I can do anything I want to you, can't I?"

"I thought that's what you wanted," Simon said, and finally he looked to her feet again. Grace laughed lightly but didn't say anything else, so he continued. "I can't help how it feels to be useful to you. I-" he swallowed and turned his gaze upward, not to peek up her clothes but to look at her face with a mad, wholehearted reverence. "I want you to make use of me. If this is what you want, what you like- then I want it too. Even if it hurts."

The earnestness with which he said such things clearly affected Grace. She glowered at him and hissed, "How dare you assume I like this how you do! This isn't like that for me, I'm not a perverted weirdo." He doubted her now, but he didn't dare to state that aloud. He'd seen the way she flushed when he cried out before, watched her gaze darken to a sultry state as his body became bruised and bloodied by the mistreatment she so happily dealt out to him. She always moved with purpose when she did these things, swayed and swaggered about him in a manner meant to tempt and titillate. The new outfit really only emphasized the dangerous, half-feral sensuality that she'd already been contributing to each session. Even if he didn't say it, though, the doubt still showed on his face as he dared to keep looking at her. "You really don't believe me, do you? Fine, you freak. We'll play this game your way." Grace spoke with restraint, and her expression grew more conflicted. She kept her cool despite the hesitation. The last thing she wanted was for him to catch onto the fact that she'd also allowed it to come this far. She crouched down and began to unbutton his pants.

"Grace, what are you-" Simon began to question. Grace slapped his face quickly.

"Shut up!" she barked. Simon went quiet, except for the way his breath hitched as she pulled down his pants and underwear, folding them over his kneepads and underneath his bent legs. Her lip curled in distaste when she found that he was already hard, the tip was shiny and slick with precum. "Gross," she muttered. "How long has it been like that?" Simon's breath heaved. He felt almost sick with embarrassment. He couldn't comprehend why she would do this, why she would take it this far. She slapped him once more, grasped him by the chin, and made him maintain eye contact as she asked the question again, slowly enough that he'd understand despite the nauseous, dark haze clouding his mind.

Simon's mouth felt dry, so he had to swallow thickly before he quietly confessed, "I could see your underwear."

"Did hitting you make it go away?" she asked next, her voice dripped with a feigned sweetness. It felt like an interrogation done under torture, especially when she leaned forward and laid her gloved hands onto his bare thighs. Her thumb was digging into the bruise that her heel had left, which wasn't an accident. She watched with a sort of detached interest at how his cock jumped when she pressed harder into the mark that was already there.

Simon shook his head, then also breathed out a quiet, remorseful, "N-no, that just makes it worse-nngh!" She'd squeezed at his cock as he spoke, cutting him off. At first, it felt incredible and his whole body started to tingle at the contact. She kept squeezing after that, though, and soon the pleasure turned into a particularly sharp and violent pain. Simon let out several high, whimpery noises as he tossed his head, too afraid of it hurting more to jerk away with his hips. Grace let out a noise like she had just discovered something new that pleased her, then abruptly let go and flicked at the tip before she finally stopped. She stood up again, with bright eyes and a predatory smirk.

"So, it really does hurt extra bad there~" she trilled. She'd heard the rumors from the other Apex boys, but hadn't had the opportunity to see just how easy it was to hurt someone in that place until now. She looked forward to the new opportunities that it provided. Despite the abuse it had already undergone, Simon's dick twitched as he shifted uncomfortably. The ropes around his wrists were chaffing at his skin by now and the sensation of having his arms held above his head had turned into a deep ache. Grace wasn't done just yet, though, so he just accepted the discomfort until it became part of the pleasure, knowing that she wanted him just like this, breathless and teary-eyed and trussed up so he couldn't escape even if he wanted to. He nearly began crying again when she delicately placed the toe of the heel she wore along the length of his hard dick to pin it to the floor, with just enough of a threat in her wicked smile to make him nervous.

"Grace, ma'am," he panted, staring at her foot with wide eyes, "please..."

"Please? Please don't? Or maybe," the pressure on his dick increased just slightly, which made him whimper. The force she was using made it start to hurt again, badly enough to make him go completely still. "Maybe you're begging for me to do it. Which is it, Simon?" she asked.

"I-" Simon had trouble answering, because as sick and weird and wrong as the idea was he couldn't deny that there was a part of him that was curious. Stronger still was the part of him that wanted to give himself over to her completely. If that meant she wanted to literally crush his dick beneath her beautiful heel, he was willing to go through it for her sake. "I don't know."

"Perverted weirdo!" she jeered at his hesitation. Her eyes sparkled and then she jerked her foot back, winding up to strike with it. Simon could have tried to move, but he just tensed up and braced himself. Even expecting it, though, he still yelped loudly when she landed the kick right between his legs with the bridge of her foot. He instinctively tried curling down into himself afterward, but that made the rope jerk on his bound arms. He hiccuped out a sob. It hurt so bad that he started to drool a bit as he tried to catch his breath, the shock zinging around in his pelvis like it couldn't escape. His arms felt taut, twisted back with how far he had lurched, but he couldn't get his torso to lift so he could ease that pressure. Out of the peripheral of his vision, he saw her rearing her foot back again and this time he couldn't help but wince, flinch, and whine pathetically in anticipation. Grace cackled at his show of fear and set her foot back down. She just wanted to see how badly he'd react to the threat of a second kick aimed there. The hungry sparkle to her eyes began to fade as she saw that he was still recoiling from the first one anyway. She hummed, and her expression became objective and calculating once more. She decided, "You know, I'm starting to get bored with this for now. And, I feel a lot better. So I'll let you down."

Simon noisily sucked at the drool hanging from his lips before he murmured, hazily, "Thank you." Grace worked at the rigging, loosening the knots that would set Simon free. As soon as the ropes around his wrists grew slack, he yanked his hands out from them and cradled his privates, wincing at how tender they felt with just the one kick. He curled into himself until his forehead was pressed to the floor and started to openly weep. The movement of leaning forward had made the sticky, congealing blood on his back pull at the welted skin from which it dripped, which added to his overall suffering.

"Ugh," Grace scoffed at the display. "I'm going to go change," she then announced, and her heels clicked as she walked briskly away from where he was prostrate, face to the floor like he was trapped deep in prayer as all of the aches and pains began to settle in at once. He couldn't stop crying, couldn't stop shaking and shivering, and just overall making a fool of himself. Grace came back out wearing her sneakers, he could tell by the softer, padded sound of her footsteps. He couldn't bring himself to look at her again, not yet. He wanted to sear the previous image of Grace into his mind first, the most vicious and cruel version he'd met yet, with the short clothes and tight nylons, the tall heels that only served to emphasize her proper place above Simon. "Whenever you get a hold of yourself," she began, once she'd paused a short distance from where he was laid out, "I could use some help with dinner." With that, she left the empty ruined store entirely.


End file.
